


That First Time

by Dolavine



Series: spn_masquerade fills [1]
Category: Supernatural RPF
Genre: Awkward Sex, Body Exploration, Dirty Talk, First Time, Hand Jobs, M/M, Underage - Freeform, Virginity, talk of masturbation
Language: English
Status: Completed
Published: 2014-08-24
Updated: 2014-08-24
Packaged: 2018-02-14 12:31:00
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 2,029
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2191935
Author URL: https://archiveofourown.org/users/Dolavine/pseuds/Dolavine
Summary: <blockquote class="userstuff">
              <p>15yr old Jensen and Jared have been best friends forever. Their friends are boasting about sexual exploration and they are still virgins. They decided to do a practice run, with each other.</p>
            </blockquote>





	That First Time

**Author's Note:**

> Written for the [kink_masquerade](http://spn-masquerade.livejournal.com) at Lj.
> 
> Prompt 1 Jensen/Jared, Underage, virginity, awkward sex  
> Jared and Jensen have been best friends forever and are both really nervous about losing their virginity, so they decide to fumble their way through it together.
> 
> Lightly beta'd.

Jared throws his book bag on Jensen’s bed then flops down next to it. “Dude, Chad was making me pretty uncomfortable with his sexcapade story.” Jared’s rummaging through his bag for a candy bar.

Jensen sits down next to him and helps him root for the candy. “He acts like he’s been fucking for years. Hell, he’s only fifteen like us.” 

Jared finds the candy and tears it open. “And it was his first time, not like he’s all that experienced with anything other than his hand, ya know.” His mouth is full of chocolate and nougat.

“Exactly!” Jensen pulls Jared’s hand and the candy bar to his mouth and takes a bite. “That guys all big talk, I wouldn’t worry about it.” He slings his arm over Jared’s shoulder and pulls him in tight. “I mean, there’s nothing wrong with being a virgin until the right guy comes along.” 

Jared looks at him with a questioning eye. “Guy?” he swallows hard.

“Person.” Jensen corrects his term. 

“Yeah.” Jared’s thought about Jensen, he thinks about how Jensen gets hard when they wrestle and how he likes it when Jensen pushes that erection against him. He even has wet dreams where he’s kissing those soft pink plush lips, but that’s all just fantasy. His heart flutters and sinks at the thought of actually doing anything about it. 

Jensen takes another bite of Jared’s candy bar and tries to push down his feelings. “I think you should have a practice buddy to… you know… practice with.”

Jared furrows his brow and takes a bite of the candy again. “Like a study partner?”

“Kind of, you know… get yourself prepared for the real thing so that you don’t make a fool of yourself when you actually do it for the first time.”

Jared thinks about that for a minute. He mulls it over as he finishes his candy bar. “That’s a really good idea.” He looks over at Jensen who’s now lying down on the bed. “Would they have to be experienced?” 

“I guess not. Maybe it could be a learning experience for them both. You know- a trial and error sort of thing.” He bites his lower lips as he thinks about what it would be like to do it with his best friend, Jared but he’s too nervous to ask.

Jared crawls over Jensen and lies down next to him- their bodies tight together on the single bed. 

They’re both staring up at the ceiling, neither saying a word, their minds working simultaneously with the same thought but neither realizes it until they both open their mouths at the same time and speak in unison. 

“Want to try it with me?” 

Jensen laughs. “Huh?” he heard Jared alright; he just wants to hear it again without his own voice.

“What?” Jared never thought Jensen was interested in him.

“Say that again.” Jensen asks, he’s looking into Jared’s eyes intensely as he waits for him to say it again.

“Um…” Jared stammers, more nervous this time. “Want to try it with me?” He can hardly keep his gaze on Jensen’s as he waits for the answer.

 

“Sure.” His heart is in his knees at the moment and he can feel his back starting to sweat.

Jared shifts in bed, rolls over and puts his hand on Jensen’s belly. “What should we do?” His voice is almost a whisper. 

“Don’t these things usually start with a kiss?” Jensen turns over so that he’s face to face with Jared. 

They’re looking into each other’s eyes, examining each other’s faces like they’ve never seen them before. 

Jensen’s hand comes up to Jared’s shoulder and he moves in a little closer. 

They stay like this for a little longer. Jared pondering what comes next, how fast to move, how to angle his head for the first kiss. Jensen wondering what it will feel like to kiss a guy. He’s kissed a few girls and he liked it but, it’s always been Jared’s mouth he’s kissed in his dreams at night. Those dreams that when he wakes up, he’s got a leaking hard on and has to rub one out to the image. 

Jensen takes a deep breath and goes in for the kiss. Jared reacts quickly moving his head in and their lips smash into each other. 

Jensen laughs through the closed mouth kiss. Jared is embarrassed that this is his first kiss and he managed to go at it like a bull in a china shop. His cheeks are hot but he doesn’t pull away because Jensen isn’t and that means something. 

Their lips are tight together, their eyes closed and Jensen starts to move his hand up Jared’s shoulder to his neck. He wants to cup his jaw like they do in the movies, give it some dramatic effect.

“Mmmm.” Jared moans through the dry chaste kiss. He feels something wet as Jensen runs his tongue over the seam of his mouth and then pushes between it. He lets him do it, enjoys the feel and wetness of the exchange. He opens his mouth slightly and lets Jensen touch his tongue, chills run through his body as he tastes his best friend’s sweet saliva and it only makes him want more.

Their bodies push close together, hips nudging as their groins slide against each other. The wet kissing is loud and sloppy but neither care, it’s making them hard and that is the desired effect. 

“Gonna touch you.” Jensen’s words are muffled as he continues to kiss Jared.

“Okay.” Jared pulls away a little bit and looks into Jensen’s eyes. “Want me to open my jeans?” He bites his kiss swollen lower lip and he suddenly feels very shy.

“Nah, gonna just put my hand down your jeans and feel things out a little.” Jensen smiles as he rucks up Jared’s t-shirt and wiggles his hand down between the loose fitting waistband and Jared’s flat pubescent abdomen. 

He’s palming Jared through his underwear. There are damp spots where Jared’s leaked precome and Jensen likes the warm wet spots, they tell him that Jared’s really worked up. He strokes him through the cotton, his fingers slipping inside of the fly seam to touch the ridged flesh of Jared’s shaft. Jared moans, and bucks his hips a little at the teasing touches as he tries very hard not to come.

“Can I touch you?” Jared’s voice is low and small, like he’s worried about rejection. 

“Of course.” Jensen is a bit more brazen. He opens his jeans and yanks them off of his hips, letting Jared see the full length of his erection.

Jared’s seen Jensen’s cock before, just never hard and he’s a bit intimidated by its thickness because his is long and thin. “Nice.” He compliments him.

“Thanks.” Jensen smiles shyly. “Yours feels really long.” He wants to see it but doesn’t want to scare Jared by yanking it out.

“Want to see it?” Jared starts to undo his jeans.

“Absolutely.” Jensen smiles, pulls his hand out and waits for Jared.

Jared pulls everything down, his briefs and his jeans; his cock falls to the side. It’s long, longer than Jensen’s seen on anyone that isn’t in the porn industry. 

He swallows dryly and looks up into Jared’s eyes. “God, that’s beautiful.” He hears himself say it and can’t believe that he did. His cheeks turn pink with embarrassment and Jensen never gets embarrassed about anything.

Jared makes a nervous chuckling sound then looks away. “Thanks,” he says quietly.

Jensen starts to stroke Jared’s cock. At first its loose strokes, slow and soft but as Jared’s hips start moving with him, he increases the speed and roughness.

 

“Is this how you jerk off?” Jared asks with innocence in his voice.

“Yeah, sorta.” Jensen twists the head and Jared moans louder this time.

“Christ!” It’s almost a scream but Jared quickly tones it down. “Show me how you jerk off.” He says once he gets control of his tone again.

“I’m usually naked.” Jensen has a sly grin as he thinks about getting Jared completely naked.

Jared’s eyes go wide. He’s always been self-conscious about his slender build. “Only if you’re naked too.” Jensen being naked would help to ease his nervousness- _maybe_.

“For sure.” Jensen gets up and starts to strip. 

Jared watches him, eyes transfixed on every little movement as he pulls his t-shirt off, then finishes taking off his jeans and underwear. He notices Jensen’s freckles. He’s seen them before but he’s never _seen_ them before. He has them everywhere, even on his dick.

When Jensen’s naked he smiles at Jared. “Your turn.” He strokes his cock a few times to keep it nice and hard.

Jared swallows hard then gets up and strips down.

Jensen is observing, his eyes catching every inch of Jared’s long lean body. His gangly arms and legs are fumbling awkwardly as he pulls his clothes off of them. He reaches over and runs his hands along Jared’s flanks down to the thick cut of his hipbones. 

“Sorry, I’m so skinny.” Jared’s arms move over his body.

“You’re perfect.” Jensen pulls him in and kisses him again. Their cocks bump off of each other, sending sensations rushing through their bodies.

Jensen backs Jared up against the bed then leans him back so that he can crawl over him. His naked body straddling Jared’s thin hips, his crotch resting over Jared’s as their cocks nestle next to each other. He’s running his hands down over Jared’s sternum over the bumps of his rib cage and ending at the soft line of pubic hair just above his leaking cock.

Jared’s enjoying the soft touches, his body responds with soft intakes of breath as he hollows out his abdomen when he sucks in forcefully with pleasure then exhales slowly. 

Jensen starts to grind down on Jared’s cock. “Does it feel good?” he’s grasping both of their cocks in one hand.

“Uh, huh.” Jared nods emphatically. 

“Good.” He starts stroking as he grinds down. Their balls are rubbing together with each circle of his hips.

Jared’s hands come up and take hold of Jensen’s hips. “You do this to yourself?” His words are breathy with want and need.

“Over a pillow as I jerk off.” His words are broken. The feel of Jared’s hard cock sliding against his, his hand working over them both at the same time, is almost too much for him, and Jensen has always prided himself on being able to come on command or hold out for a long time and just enjoy his masturbation skills. But Jared’s body is breaking all of his rules of control.

“Cool.” Jared pushes back, his body is getting hot, his guts swirling with that feeling of intense pleasure and he knows he can’t hold out any longer. “Gonna come.” He warns Jensen.

Jensen’s glad because he’s about to come too. “Let it go.” He says in a husky tone as he increases the speed and squeezes their heads a little tighter.

Jared closes his eyes and squeezes Jansen’s hips so tight that his nails dig into the skin. He bucks up and grunts as he spills out hot and thick. The come shooting into the air in forceful spurts.

Jensen loves it; he follows Jared over the edge. He rocks harder down onto Jared as he feels his balls tighten and pull up. His cock jerks and a stream of creamy jizz shoots out only to land on Jared’s cheek. He spurts out waves of come, spraying Jared’s chest with thick ribbons.

Jared’s breathless, his body hot and buzzing as he feels Jensen fall forward onto him. 

“That was, intense.” Jensen says into Jared’s neck. His body is smearing their release between them.

“Better than I could have ever hoped it would be.” Jared puts his fingers through the soft spikes of Jensen’s hair. 

“We’ll only get better as we practice.” Jensen smiles into Jared’s shoulder.

Jared’s mouth spreads wide with an elated smile. “Yes, practice, more practice.”

“Practice makes perfect, or so they say.” Jensen kisses the long leader of Jared’s neck before nuzzling in completely.

The End


End file.
